Business was a way for men to talk about their feelings. The internet was choked with blindly ambitious and professionally inexperienced men giving each other anecdote-based instruction and bullet-point advice. 10 Essential Startup Lessons You Won’t Learn in School. 10 Things Every Successful Entrepreneur Knows. 5 Ways to Stay Humble. Why the Market Always Wins. Why the Customer Is Never Right. How to Deal with Failure. How to Fail Better. How to Fail Up. How to Debug Your Anger. How to Build Workarounds for Your Emotions. How to A/B Test Your Kids. 18 Platitudes to Tape Above Your Computer. Raise Your Way to Emotional Acuity. How to Love Something That Doesn’t Love You Back.
One afternoon, I wandered into a fast-food restaurant during lunch and found the CEO sitting by himself, eating a veggie burger and looking at his phone. I sat down and he slid his fries across the table. He was reading a book by one of our investors, he said. I was familiar with it. The book offered guidance on how to navigate the choppy waters of entrepreneurship and conquer the twin demons of self-doubt and external pressure. It spoke of learnings, battles, journeys. Every chapter opened with an epigraph from a rap song. The struggle was real.
The men whom the CEO seemed to admire were the same men whom all the other men in the ecosystem admired: entrepreneurs, investors, one another. Chief among them was a founder of the seed accelerator, an English computer scientist who was the startup ecosystem’s closest thing to an intellectual. An aphorism generator who blogged prolifically, his rhetorical style was cool, rational, and unemotional. He pontificated, at length, on intellectual conformity. He was prone to making favorable comparisons between startup founders and great men of history: Milton, Picasso, Galileo. I didn’t doubt his business insight, but I didn’t know why he seemed to believe it qualified him as an expert on anything—everything—else.
I had compassion for anyone who was trying to figure it out, and there was a part of me that sympathized with the CEO: though he would never admit it, he must have been in over his head. Still, I couldn’t imagine modeling my own life after that of a venture capitalist—couldn’t imagine reading a book simply because a financial middleman I’d never met had recommended it. Of course, they weren’t just figureheads to the CEO, who knew them personally.
The book was good, the CEO told me. If you like this, you’ll love therapy, I did not say. I looked at his phone. He was on the first page of a chapter titled “Preparing to Fire an Executive.”
“That’s a coincidence,” he said, meeting my eyes. “Don’t take it too seriously, or seriously at all.” Firing people was horrible, he told me. It was like going through a bad breakup, but worse—agonizing. I told him not to worry; it was just a book.
I couldn’t have taken it seriously, anyway. As things were, the CEO was also the president and the chairman of the board. He oversaw Product, Engineering, Solutions, Marketing. He was the only true executive we had.
Noah and I met for drinks in SoMa, a few blocks from the office. The bar smelled like a deep fryer, and a fleet of motorcycles hung from the ceiling. I hadn’t seen him since he had been fired, and I was nervous: What if he blamed me? We embraced like long-separated family members.
Noah looked happier—relieved. His Australian work boots had dirt on them. He was sleeping better, he said. He was thinking about opening a worker-owned bagel shop—cooperatives were the only ethical business model—and trying to remove the word “app” from his vocabulary. “Ap-pli-ca-tion,” Noah said, correcting himself. “The abbreviation obscures that it’s software.” This was deliberate and nefarious, reflected in the colorful, cartoonish designs of even the most technically sophisticated programs. “We’re not software!” he chirped. “We’re your friends!”
I offered a debrief on the startup: growth was hard, revenue was flowing, Tahoe was weird, we missed him. We rehashed his firing in lurid detail. The office was starting to feel really claustrophobic and air-conditioned and sterile, he said. His job responsibilities hadn’t changed. “I thought, If I’m going to do this job forever, I’d better be rich in five years,” he said. “I wanted to get paid out. I was employee thirteen. I wanted to work there, I wanted to work hard, but I wanted to make sure at the end of it I had a significant percentage of the company.”
I was reminded, not for the first or last time, that my stake in the company was minuscule. When I had signed the offer letter, the number of shares sounded high, but I hadn’t known to ask the size of the option pool. In a decent acquisition, I might net ten thousand dollars. I pulled on my beer, hard.
Noah paused and looked up at the bikes, then back at me. “You could describe my position as totally unreasonable,” he said. “Or you could say what I asked for was what I needed, which was just a shitload more than what they were willing to give.”
In any case, he said, at least his conscience was clearer. I asked what he meant.
“Come on,” he said. “We worked at a surveillance company.” He brought up the NSA whistleblower, who was back in the media. More revelations were coming out—nearly two hundred thousand documents had been released. The surveillance apparatus was larger and more complex than originally reported, and Silicon Valley was deeply implicated. “I didn’t think about it while I was working there, because the product is so business oriented,” Noah said. “I didn’t necessarily see it as a problem for society. Plus, I don’t think I had the information that all the money from the internet comes from surveillance.”
By surveillance, I clarified, was he just talking about ad tech? I found digital advertising annoying, but I had never thought of it as particularly malicious—though it was clear from our customer companies that free services usually meant users were being exploited in one way or another. The most straightforward way to exploit them, naturally, was through rapacious data collection.
“I don’t see a difference between the two, functionally,” Noah said. “We facilitated the collection of the information, and we have no idea how it will be used and by whom. For all we know, we could have been one subpoena away from collaborating with intelligence agencies. If the reports are accurate, the veil between ad tech and state surveillance is very thin.”
I didn’t know how to respond. I didn’t want to correct him. It was perhaps a symptom of my myopia, my sense of security, that I was not thinking about data collection as one of the moral quandaries of our time. For all the industry’s talk about scale, and changing the world, I was not thinking about the broader implications. I was hardly thinking about the world at all.
I went to the symphony with my friend Parker, a digital-rights activist I knew from New York. Parker worked for a nonprofit focused on digital civil liberties—privacy, free expression, fair use—that had been founded in the nineties by utopian technologists with a cyberlibertarian bent. It was, in a sense, the ecosystem’s anchor to history. The office was cluttered with dusty servers and outdated computers running creaky open-source software. People who really cared about technology, he had once explained to me, never used anything new. The default attitude was distrust.
Years prior, we had conducted an off-again, on-again, casual noncommitment, which had mostly consisted of him explaining things and then apologizing. “Email is about as secure as a postcard,” he’d remind me, as we wandered between families at the farmers market in Fort Greene Park. “You don’t expect your mailman to read it, but he could.” I had listened patiently as he tried to teach me about cryptocurrencies and the promise of the blockchain, the shortcomings of two-factor authentication, the necessity of end-to-end encryption, the inevitability of data breaches.
The romance didn’t last, but in its wake we had fallen into a rhythm of exchanging insecure emails on niche topics, like 1980s interface design, binary code, and public-domain art, and occasionally meeting for chaste, geriatric cultural activities.
The concert hall was a quarter full. As the lights dimmed, I made a silent promise that I would spend more time and money at San Francisco’s older cultural institutions. I would participate in the civic life of the city where I lived. I would surrender my New York State driver’s license. I would look up who the mayor was.
During intermission, we drank plastic cups of white wine and split a bag of candy. Parker was stressed about the erosion of net neutrality. He was working on a campaign to galvanize tech workers, but it wasn’t gaining traction the way he had thought it would. I knew something about net neutrality already, but I let him explain it to me anyway. Nostalgia; old times’ sake.
The problem, he said, was that the most important issues facing the tech industry were also the most tedious. It was in their interest to fight, but founders and tech workers didn’t know how to organize. They didn’t have the patience to lobby. They didn’t consider their work political. “They all assume this will just last forever,” he said.
We watched an elegant older couple drift by, properly dressed for a night out. I felt a little guilty for ruining their scenery. “The worst part,” Parker said, “is that the technology is getting worse every day. It’s getting less secure, less autonomous, more centralized, more surveilled. Every single tech company is pushing on one of those axes, in the wrong direction.”
My throat felt like acid. Hey, I said, and paused. Parker looked over at me. Sugar dotted his lower lip. Do you think I work at a surveillance company? I asked.
“What a great question,” he said. “I thought you’d never ask.”